WO1994008991A1 - Herbicidal pyrazolyloxy-picolinamides - Google Patents

Herbicidal pyrazolyloxy-picolinamides Download PDF

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Publication number
WO1994008991A1
WO1994008991A1 PCT/EP1993/002925 EP9302925W WO9408991A1 WO 1994008991 A1 WO1994008991 A1 WO 1994008991A1 EP 9302925 W EP9302925 W EP 9302925W WO 9408991 A1 WO9408991 A1 WO 9408991A1
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WO
WIPO (PCT)
Prior art keywords
group
yloxy
pyrazol
alkyl
general formula
Prior art date
Application number
PCT/EP1993/002925
Other languages
English (en)
French (fr)
Inventor
Axel Kleemann
Robert John Griffith Searle
Original Assignee
Shell Internationale Research Maatschappij B.V.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to RO95-00739A priority Critical patent/RO113989B1/ro
Priority to PL93308484A priority patent/PL175464B1/pl
Priority to DE69303721T priority patent/DE69303721T2/de
Priority to MD96-0316A priority patent/MD1762B2/ro
Priority to GEAP19932612A priority patent/GEP19981225B/en
Priority to DK93923530.5T priority patent/DK0665841T3/da
Priority to SK520-95A priority patent/SK281197B6/sk
Priority to BR9307288A priority patent/BR9307288A/pt
Priority to CA002142463A priority patent/CA2142463C/en
Application filed by Shell Internationale Research Maatschappij B.V. filed Critical Shell Internationale Research Maatschappij B.V.
Priority to TJ96000387A priority patent/TJ330B/xx
Priority to JP50965994A priority patent/JP3485185B2/ja
Priority to RU95109933A priority patent/RU2130021C1/ru
Priority to EP93923530A priority patent/EP0665841B1/en
Priority to US08/325,173 priority patent/US5707932A/en
Priority to UA95048345A priority patent/UA44695C2/uk
Priority to AU53365/94A priority patent/AU675677B2/en
Publication of WO1994008991A1 publication Critical patent/WO1994008991A1/en
Priority to GR960401183T priority patent/GR3021390T3/el

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the invention relates to certain pyrazolyloxy-picolinamide derivatives, processes for their preparation, compositions contain ⁇ ing such compounds and their use as herbicides to combat undesired plant growth.
  • Diflufenican [N-(2,4-difluoro-phenyl)- -2- (3-trifluorometh lphenoxy)-3-pyridine carboxamide] was subse ⁇ quently developed, by a different research group, as a commercial herbicide for use against broad-leaved weeds in winter cereals, such as winter wheat and barley.
  • U.S. Patent Specification No. 4 251 263 is concerned with the N-alkyl amides of Gutman, and related N-alkenyl and N-alkynyl amides.
  • the compound documented as being the most active of the aliphatic amides prepared and tested is N-(1,l-dimethylprop-2- ynyl) -2- (3-trifluoromethylphenoxy)-3-pyridine carboxamide, which gives 85% control preemergence and only 57% control postemergence on specified narrow- and broad-leaved species.
  • Z represents an oxygen or sulphur atom
  • R 1 and R 2 each independently represents a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, alkaryl, hydroxy, alkoxy, alkenyloxy, alkynyloxy, alkylcarbonyl, amino, mono- or di- alkylamino, alkoxycarbonylamino, arylamino, arylalkylamino or dialkylcarbamoyl group, or together represent an alkylene chain which is optionally interrupted by an oxygen or sulphur atom or by a group -NR- in which R represents a hydrogen atom or an alkyl group, R 3 or each R 3 independently represents a halogen atom or an alkyl, alkoxy, alkylthio, dialkylamino or haloalkyl group,
  • R , R and R each independently represents a hydrogen or halogen atom, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, alkaryl, alkoxy, amino, mono- or di-alkylamino, alkoxycarbonylamino, arylamino, dialkylcarbamoyl, acyl or acyla ido group or a cyano group, with the proviso that R and R do not represent an acyl, acylamido or cyano group, and n represents 0, 1, 2 or 3.
  • the invention especially relates to compounds of the general formula I in which any alkyl, alkenyl, alkynyl part- of any of the substituents R to R contains up to 12 carbon atoms , preferably up to 10 carbon atoms, any cycloalkyl part of any of the substituents R to R contains from 3 to 10 carbon atoms , preferably from 3 to 8 carbon atoms, any alkylene chain, optionally interrupted by an oxygen or sulphur atom or by a group -NR- in which R represents a hydrogen atom or an alkyl group, contains from 2 to 8 chain mem ⁇ bers, preferably from 2 to 6 chain members and any aryl part of any of the substituents R to R contains 6, 10 or 14 carbon atoms, preferably 6 or 10 carbon atoms, and in which each optionally substituted group independently is substituted by one or more halogen atoms or nitro, cyano, alkyl, preferably C. . alkyl, haloalkyl,
  • Optionally substituted amino groups include amino groups substitut ⁇ ed by one or two groups selected from alkyl, aryl, cycloalkyl, cycloalkylalkyl, arylalkyl and aralkyl groups, in particular alkylamino, dialkylamino, arylmethylamino and arylamino.
  • Any acyl group includes formyl, optionally substituted alkyl carbonyl and optionally substituted aryl carbonyl groups.
  • Any alkyl, alkenyl or alkynyl group may be linear or branched.
  • Preferred alkyl substituents are at least methyl, ethyl, propyl, butyl and pentyl.
  • a preferred aryl substituent is a phenyl group.
  • a halogen atom suitably denotes a fluorine, chlorine or bromine atom.
  • the invention especially relates to compounds of the general formula I in which Z represents an oxygen atom.
  • the invention especially relates to compounds of the general
  • R and R each independently represents a hydrogen atom or a C. regularly alkyl, C. . alkenyl, C. ⁇ alkynyl,
  • R represents a C. , alkyl, C. , alkenyl, C. . alkynyl, C. , cycloalkyl, phenyl, benzyl, C. alkylamino, C. , dialkylamino or phenylamino group, each group optionally substituted by one or more fluorine, chlorine or bromine atoms, especially fluorine or chlorine atoms, or a
  • the invention especially relates to compounds of the general
  • the substituent(s) R may be at any free position or combination of positions on the pyridyl ring. A preferred position is the 4-position.
  • the invention further especially relates to compounds of the general formula I in which R , R and R each independently repre ⁇ sents a hydrogen atom, a cyano group or a C. , alkyl, C_ , cycloalkyl, C. , acyl, C. alkenyl, phenyl or naphthyl group, each group optionally substituted by one or more halogen atoms, especially fluorine atoms, or C- , alkyl, C. , haloalkyl, C. , alkoxy, C. , alkylamino, C. . dialkylamino or aryl amino groups.
  • the invention also especially relates to compounds of the
  • R represents a hydrogen atom, a C. alkyl group or a phenyl group optionally substituted by a halogen atom
  • R represents a hydrogen atom or a C. , alkyl or phenyl group, each group optionally substituted by one or more halogen atoms, especially fluorine atoms, or represents a C cycloalkyl
  • R represents a hydrogen atom or a C_. , alkyl group, optionally substituted by one or more halogen atoms.
  • the invention especially relates to compounds of the general formula I in which n represents 0 or 1.
  • a particularly preferred sub-group of compounds of the general formula I is that in which R represents a methyl, ethyl, propyl, allyl, butyl, pentyl, including neopentyl, methylallyl, propynyl, dimethylpropynyl, methoxyethyl, cyanomethyl, cyclopropyl, cyclobutyl, cyclopentyl, chloroethyl, trifluoroethyl, cyclopropyl- methyl, dichlorocyclopropylmethyl, t-butoxy, phenyl-, fluorophenyl, difluorophenyl, trifluoroethylamino, butylamino, dimethylamino, phenylamino or fluorophenylamino group.
  • Another particularly preferred sub-group of compounds of the general formula I is that 2 in which R represents hydrogen, methyl, ethyl, propyl, butyl,
  • R 4 represents methyl, ethyl or phenyl
  • R5 represents hydrogen, methyl, trifluoromethyl, ethyl, propyl, butyl, phenyl or cyclopropyl, and in which R represents hydrogen or methyl.
  • the present invention also provides a process for the prepara ⁇ tion of compounds of the general formula I as defined hereinbefore, which comprises reacting a compound of the general formula II, or an activated derivative thereof,
  • a leaving group is any group that will, under the reaction conditions, cleave from the starting material, thus enabling substitution at that specific site.
  • the leaving group Q may suitably be a halogen atom, for example a bromine atom or, espe ⁇ cially, a chlorine atom, an alkoxy group, suitably C. , alkoxy, especially methoxy, an alkyl- or aryl-sulphonium group, especially a C. alkyl-, phenyl- or tolyl-sulphonium group, or an alkyl- or aryl-sulphonic acid group, especially a C. , alkyl-, phenyl- or tolyl-sulphonium group.
  • Activated derivatives of the compounds of the general formula II are compounds in which the hydroxy group of the acid function has been replaced by a suitable leaving group, for instance a halogen atom, for example a bromine atom, or especially, a chlorine atom, an alkoxy group, suitably C. , alkoxy, especially methoxy, or an imidazole group.
  • a suitable leaving group for instance a halogen atom, for example a bromine atom, or especially, a chlorine atom, an alkoxy group, suitably C. , alkoxy, especially methoxy, or an imidazole group.
  • the process is suitably carried out in the presence of an organic solvent, for example dimethylformamide or dimethylsulphoxide, or an aromatic hydrocarbon, for example benzene or toluene, or a halogenated hydrocarbon, for example dichloromethane, or an ether, for example diethyl ether, or an ester, for example ethyl acetate.
  • an organic solvent for example dimethylformamide or dimethylsulphoxide
  • an aromatic hydrocarbon for example benzene or toluene
  • a halogenated hydrocarbon for example dichloromethane
  • an ether for example diethyl ether
  • an ester for example ethyl acetate.
  • the process is suitably carried out at a temperature in the range of 0 to 100 °C, preferably at the reflux temperature of the reaction mixture, and suitably in the presence of a base, for example potassium hydroxide, and a copper catalyst, such as cuprous chloride.
  • a base for example potassium hydroxide
  • a copper catalyst such as cuprous chloride.
  • reaction is carried out using substantially equimolar amounts of the reactants.
  • Z represents a sulphur atom
  • Compounds of the general formula I in which Z represents a sulphur atom are suitably prepared by reaction of a compound of the general formula I, or a precursor thereof, later on followed by one or more additional reactions, in which Z represents an oxygen atom, with phosphorous pentasulphide under standard reaction conditions, for example by heating, suitably under reflux, in the presence of an inert organic solvent, suitably an organic solvent, for example benzene, toluene, pyridine or quinoline.
  • the compounds of the present invention may be isolated and purified by conventional techniques, for example by solvent extrac- tion, evaporation followed by recrystallisation or by chromatography on for example silica or alumina.
  • the conversion of a resultant compound of the general formula I into a further compound of the general formula I may suitably be carried out by reaction with an alkyl halide.
  • the alkyl halide is an alkyl iodide, bromide or chloride.
  • reaction of the compounds obtained by reaction of com ⁇ pounds of the general formula II in which Q represents a leaving group, with a substituted hydroxypyrazole is suitably carried out in the presence of an organic solvent, for example dimethylformamide or dimethylsulphoxide, or an aromatic hydrocar ⁇ bon, for example benzene or toluene, or a halogenated hydrocarbon, for example dichloromethane, or an ether, for example diethyl ether, or an ester, for example ethyl acetate.
  • an organic solvent for example dimethylformamide or dimethylsulphoxide
  • an aromatic hydrocar ⁇ bon for example benzene or toluene
  • a halogenated hydrocarbon for example dichloromethane
  • an ether for example diethyl ether
  • ester for example ethyl acetate.
  • the process is suitably carried out at a temperature in the range of 0 to 100 °C, preferably at the reflux temperature of the reaction mixture, and suitably in the presence of a base, for example potassium hydroxide, and a copper catalyst, such as cuprous chloride.
  • a base for example potassium hydroxide
  • a copper catalyst such as cuprous chloride.
  • Activated derivatives of compounds of the general formula II may be prepared from the corresponding acids by standard methods for the preparation of, for example, esters, using, for example alcohols and acid catalysts or thionyl chloride, or of acid chlorides and bromides, using, for example, thionyl chloride or thionyl bromide, or of imidazole derivatives, using, for example, carbonyl diimidazole.
  • the acid compounds themselves can be prepared by standard methods from chloropicolinic acid or esters thereof.
  • the substituted amines of the general formula III are either known or can be prepared by standard techniques.
  • R to R and n are as defined above.
  • This reaction is suitably carried out in the presence of an solvent such as water or ethylene glycol, using as reactants acids such as hydrochloric acid, sulphuric acid or bases such as potassium or sodium hydroxide, at a temperature in the range of 0-150 °C.
  • Compounds of the general formula V have been found to exhibit herbicidal activity and form another aspect of the invention.
  • Compounds of general formula V may be prepared by reaction of a compound of the general formula
  • the process is suitably carried out in the presence of an organic solvent, for example dimethylformamide, preferably at the reflux temperature of the reaction mixture, and suitably in the presence of a base, for example potassium carbonate.
  • an organic solvent for example dimethylformamide
  • a base for example potassium carbonate.
  • the compounds of the invention have been found to have a surprisingly high herbicidal activity with a wide spectrum of activity against grasses and, especially, broadleaved weeds. Examples have been found to show selectivity to cereals, for example maize, wheat, barley and rice, and to broad-leaved crops, for example soya, sunflower and cotton, indicating that they may be useful in combating weeds growing in such crops.
  • the invention further provides a herbicidal composition
  • a herbicidal composition comprising a compound of formula I or a compound of formula V as defined above in association with a carrier, and a method of making such a composition which comprises bringing a compound of formula I or a compound of formula V into association with a carrier.
  • the invention also provides the use of such a compound or composition according to the invention as a herbicide. Further in accordance with the invention there is provided a method of combat ⁇ ing undesired plant growth at a locus by treating the locus with a compound or composition according to the invention.
  • Application to the locus may be pre-emergence or post-emergence.
  • the dosage of active ingredient used may, for example, be in the range of from 0.01 to 10 kg/ha, suitably 0.05 to 4 kg/ha.
  • the locus may, for example, be the soil or plants in a crop area, typical crops being cereals such as wheat and barley, and broad-leaved crops, such as soya, sunflower and cotton.
  • a carrier in a composition according to the invention is any material with which the active ingredient is formulated to facilitate application to the locus to be treated, which may for example be a plant, seed or soil, or to facilitate storage, trans ⁇ port or handling.
  • a carrier may be a solid or a liquid, including a material which is normally gaseous but which has been compressed to form a liquid, and any of the carriers normally used in formu ⁇ lating herbicidal compositions may be used.
  • composi- tions according to the invention contain 0.5 to 95% -by weight of active ingredient.
  • Suitable solid carriers include natural and synthetic clays and silicates, for example natural silicas such as diatomaceous earths; magnesium silicates, for example talcs; magnesium aluminium silicates, for example attapulgites and vermiculites; aluminium silicates, for example kaolinites, montmorillonites and micas; calcium carbonate; calcium sulphate; ammonium sulphate; synthetic hydrated silicon oxides and synthetic calcium or aluminium sili- cates; elements, for example carbon and sulphur; natural and synthetic resins, for example coumarone resins, polyvinyl chloride, and styrene polymers and copolymers; solid polychlorophenols; bitumen; waxes; and solid fertilisers, for example superphosphates.
  • natural silicas such as diatomaceous earths
  • magnesium silicates for example talcs
  • magnesium aluminium silicates for example attapulgites and vermiculites
  • aluminium silicates for example kaolin
  • Suitable liquid carriers include water; alcohols, for example isopropanol and glycols; ketones, for example acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethers; aromatic or araliphatic hydrocarbons, for example benzene, toluene and xylene; petroleum fractions, for example kerosine and light mineral oils; chlorinated hydrocarbons, for example carbon tetrachloride, perchloroethylene and trichloroethane. Mixtures of different liquids are often suitable.
  • compositions are often formulated and transported in a concentrated form which is subsequently diluted by the user before application.
  • a carrier which is a surface-active agent facilitates this process of dilu ⁇ tion.
  • at least one carrier in a composition according to the invention is a surface-active agent.
  • the composition may contain at least two carriers, at least one of which is a surface-active agent.
  • a surface-active agent may be an emulsifying agent, a dispers ⁇ ing agent or a wetting agent; it may be nonionic or ionic.
  • suitable surface-active agents include the sodium or calcium salts of polyacrylic acids and lignin sulphonic acids; the condensation products of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitol, sucrose or pentaerythritol; condensates of these with ethylene oxide and/or propylene oxide; condensation products of fatty alcohol or alkyl phenols, for example ⁇ _-octylphenol or £-octylcresol, with ethylene oxide and/or propylene oxide; sulphates or sulphonates of these condensation products; alkali or alkaline earth metal salts, preferably sodium salts, of sulphuric or sulphonic acid esters containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulphate, sodium secondary
  • alkyl sulphates sodium salts of sulphonated castor oil, and sodium alkylaryl sulphonates such as dodecylbenzene sulphonate; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.
  • compositions of the invention may for example be formulat- l- 3 ed as wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates and aerosols.
  • Wettable powders usually contain 25, 50 or 75% w of active ingre ⁇ host and usually contain in addition to solid inert carrier, 3-10% w of a dispersing agent and, where necessary, 0-10% w of
  • Dusts are usually formulated as a dust concentrate having a similar composition to that of a wettable powder but without a dispersant, and are diluted in the field with further solid carrier to give a composition usually containing h-10% w of active ingredi- 5 ent.
  • Granules are usually prepared to have a size between 10 and 100 BS mesh (1.676 - 0.152 mm), and may be manufactured by agglomeration or impregnation techniques. Generally, granules will contain ⁇ -75% w active ingredient and 0-10% w of additives such as stabilisers, surfactants, slow release modifiers and binding agents.
  • Emulsifiable concentrates consist of relatively small granules having a relatively high concentration of active ingredient.
  • Emulsifiable concentrates usually contain, in addition to a solvent and, when necessary, co-solvent, 10-50% w/v active ingredient, 2-20% w/v emulsifiers and 0-20% w/v of other additives 3 such as stabilisers, penetrants and corrosion inhibitors.
  • Suspen- sion concentrates are usually compounded so as to obtain a stable, non-sedimenting flowable product and usually contain 10-75% w active ingredient, 0.5-15% w of dispersing agents, 0.1-10% w of suspending agents such as protective colloids and thixotropic agents, 0-10% w of other additives such as defoamers, corrosion inhibitors, stabilisers, penetrants and stickers, and water or an organic liquid in which the active ingredient is substantially insoluble; certain organic solids or inorganic salts may be present dissolved in the formulation to assist in preventing sedimentation or as anti-freeze agents for water.
  • Aqueous dispersions and emulsions for example compositions obtained by diluting a wettable powder or a concentrate according to the invention with water, also lie within the scope of the invention.
  • the said emulsions may be of the water-in-oil or of the oil-in-water type, and may have a thick 'mayonnaise' -like consist ⁇ ency.
  • composition of the invention may also contain other ingredients, for example compounds possessing insecticidal or fungicidal properties or other herbicides.
  • the following Examples illustrate the invention; Examples 1 to 9 illustrate the preparation of intermediates of general formula IV; Examples 41 to 52 illustrate the preparation of intermediates of general formula V; Examples 53 to 59 illustrate the preparation of intermediates of general formula VI; and Examples 10 to 40 and 60 to 177 illustrate the preparation of compounds of general formula I. All structures were confirmed by mass spectroscopy and/or 300'H nmr.
  • the tests fall into two categories, pre-emergence and post- emergence.
  • the pre-emergence tests involved spraying a liquid formulation of the compound onto the soil in which the seeds of the plant species mentioned above had recently been sown.
  • the post- emergence tests involved two types of test, viz., soil drench and foliar spray tests. In the soil drench tests the soil in which the seedling plants of the above species were growing was drenched with a liquid formulation containing a compound of the invention, and in the foliar spray tests the seedling plants were sprayed with such a formulation.
  • the soil used in the tests was a prepared horticultural loam.
  • the formulations used in the tests were prepared from solu ⁇ tions of the test compounds in acetone containing 0.4% by weight of an alkylphenol/ethylene oxide condensate available under the trade mark TRITON X-155. These acetone solutions were diluted with water and the resulting formulations applied at dosage levels correspond ⁇ ing to 5 kg or 1 kg of active material per hectare in a volume equivalent to 600 litres per hectare in the soil spray and foliar spray test, and at a dosage of level equivalent to 10 kilograms of active material per hectare in a volume equivalent to approximately 3,000 litres per hectare in the soil drench tests. In the pre-emergence tests untreated sown soil and in the post-emergence tests untreated soil bearing seedling plants were used as controls.
  • the herbicidal effects of the test compounds were assessed visually twelve days after spraying the foliage and the soil, and thirteen days after drenching the soil and were recorded on a 0-9 scale.
  • a rating 0 indicates growth as untreated control, a rating 9 indicates death.
  • An increase of 1 unit on the linear scale approximates to a 10% increase in the level of effect.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
PCT/EP1993/002925 1992-10-22 1993-10-21 Herbicidal pyrazolyloxy-picolinamides WO1994008991A1 (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
CA002142463A CA2142463C (en) 1992-10-22 1993-10-21 Herbicidal pyrazolyloxy-picolinamides
DE69303721T DE69303721T2 (de) 1992-10-22 1993-10-21 Herbizide pyranolyloxy-picolinamide
TJ96000387A TJ330B (en) 1992-10-22 1993-10-21 Herbicidal picolinamides derivatives herbicides composition a method for the control of undesired plant growth
GEAP19932612A GEP19981225B (en) 1992-10-22 1993-10-21 Herbicidal Picolinamide Derivatives
DK93923530.5T DK0665841T3 (da) 1992-10-22 1993-10-21 Herbicide pyrazolyloxy-picolinamider
SK520-95A SK281197B6 (sk) 1992-10-22 1993-10-21 Pyrazolyloxypikolínamidové deriváty, spôsob ich výroby, použité medziprodukty, herbicídna kompozícia obsahujúca pyrazolyloxypikolínamidové deriváty a jej herbicídne použitie
BR9307288A BR9307288A (pt) 1992-10-22 1993-10-21 Composto processo para a preparação do mesmo composição herbicida e processo de combate de crescimento de vegetais indesejáveis num local
RO95-00739A RO113989B1 (ro) 1992-10-22 1993-10-21 Derivati de pirazoliloxipicolinamida, procedeu pentru prepararea acestora, intermediari de sinteza, compozitie erbicida si metoda pentru combaterea cresterii plantelor nedorite
MD96-0316A MD1762B2 (ro) 1992-10-22 1993-10-21 Derivaţi de pirazoliloxipiridină, procedeu de obţinere a lor, compoziţie erbicidă, procedeu de combatere a plantelor indezirabile
PL93308484A PL175464B1 (pl) 1992-10-22 1993-10-21 Chwastobójcze pochodne pirazoliloksypikolinoamidu oraz sposób ich wytwarzania
JP50965994A JP3485185B2 (ja) 1992-10-22 1993-10-21 除草性ピコリンアミド誘導体
RU95109933A RU2130021C1 (ru) 1992-10-22 1993-10-21 Производные пиколинамида, способ их получения, производные пиридин-6-карбонитрила, гербицидная композиция, способ борьбы с нежелательной растительностью
EP93923530A EP0665841B1 (en) 1992-10-22 1993-10-21 Herbicidal pyrazolyloxy-picolinamides
US08/325,173 US5707932A (en) 1992-10-22 1993-10-21 Herbicidal picolinamide derivatives
UA95048345A UA44695C2 (uk) 1992-10-22 1993-10-21 Похідні піколінаміду, спосіб їх одержання, проміжні сполуки, гербіцидна композиція, спосіб боротьби з небажаною рослинністю
AU53365/94A AU675677B2 (en) 1992-10-22 1993-10-21 Herbicidal pyrazolyloxy-picolinamides
GR960401183T GR3021390T3 (en) 1992-10-22 1996-10-17 Herbicidal pyrazolyloxy-picolinamides.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP92118039.4 1992-10-22
EP92118039 1992-10-22

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WO1994008991A1 true WO1994008991A1 (en) 1994-04-28

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US (2) US5707932A (cs)
EP (1) EP0665841B1 (cs)
JP (1) JP3485185B2 (cs)
CN (1) CN1046941C (cs)
AT (1) ATE140456T1 (cs)
AU (1) AU675677B2 (cs)
BR (1) BR9307288A (cs)
CA (1) CA2142463C (cs)
CZ (1) CZ282171B6 (cs)
DE (1) DE69303721T2 (cs)
DK (1) DK0665841T3 (cs)
EG (1) EG20290A (cs)
ES (1) ES2091044T3 (cs)
GE (1) GEP19981225B (cs)
GR (1) GR3021390T3 (cs)
HU (1) HUT70879A (cs)
IL (1) IL107335A (cs)
MD (1) MD1762B2 (cs)
MX (1) MX9306510A (cs)
PL (1) PL175464B1 (cs)
RO (1) RO113989B1 (cs)
RU (1) RU2130021C1 (cs)
SK (1) SK281197B6 (cs)
TJ (1) TJ330B (cs)
UA (1) UA44695C2 (cs)
WO (1) WO1994008991A1 (cs)
ZA (1) ZA937781B (cs)

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WO1998004548A3 (en) * 1996-07-30 1998-03-26 American Cyanamid Co Trisubstituted pyridine compounds for herbicidal use
US6011052A (en) * 1996-04-30 2000-01-04 Warner-Lambert Company Pyrazolone derivatives as MCP-1 antagonists
WO2006078891A3 (en) * 2005-01-21 2006-08-24 Neurogen Corp Imidazolylmethyl and pyrazolylmethyl heteroaryl derivatives
CN105037342A (zh) * 2015-08-07 2015-11-11 华中农业大学 具有除草活性的吡唑醚类化合物及其应用
WO2022101270A1 (en) * 2020-11-16 2022-05-19 Syngenta Crop Protection Ag Herbicidal n-heteroaryl pyrazole compounds
US11993578B2 (en) * 2017-05-11 2024-05-28 Kumiai Chemical Industry Co., Ltd. Pyrazole-3-carboxylic acid amide derivative and pest control agent

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DE10130397A1 (de) * 2001-06-23 2003-01-09 Bayer Cropscience Gmbh Herbizide substituierte Pyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbzide und Pflanzenwachstumsregulatoren
WO2020258006A1 (en) * 2019-06-25 2020-12-30 Inventisbio Shanghai Ltd. Heterocyclic compounds, preparation methods therefor, and methods of uses thereof

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EP0488474A1 (en) * 1990-11-28 1992-06-03 Shell Internationale Researchmaatschappij B.V. Herbicidal carboxamide derivatives

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US4251263A (en) * 1979-09-04 1981-02-17 Stauffer Chemical Company N-substituted, 2-phenoxynicotinamide compounds and the herbicidal use thereof
EP0242573A1 (de) * 1986-03-21 1987-10-28 Bayer Ag 5-Acylamino-pyrazol-Derivate
EP0488474A1 (en) * 1990-11-28 1992-06-03 Shell Internationale Researchmaatschappij B.V. Herbicidal carboxamide derivatives

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6011052A (en) * 1996-04-30 2000-01-04 Warner-Lambert Company Pyrazolone derivatives as MCP-1 antagonists
WO1998004548A3 (en) * 1996-07-30 1998-03-26 American Cyanamid Co Trisubstituted pyridine compounds for herbicidal use
WO2006078891A3 (en) * 2005-01-21 2006-08-24 Neurogen Corp Imidazolylmethyl and pyrazolylmethyl heteroaryl derivatives
CN105037342A (zh) * 2015-08-07 2015-11-11 华中农业大学 具有除草活性的吡唑醚类化合物及其应用
US11993578B2 (en) * 2017-05-11 2024-05-28 Kumiai Chemical Industry Co., Ltd. Pyrazole-3-carboxylic acid amide derivative and pest control agent
WO2022101270A1 (en) * 2020-11-16 2022-05-19 Syngenta Crop Protection Ag Herbicidal n-heteroaryl pyrazole compounds

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ES2091044T3 (es) 1996-10-16
IL107335A (en) 1997-09-30
EG20290A (en) 1998-07-30
CN1046941C (zh) 1999-12-01
AU675677B2 (en) 1997-02-13
CA2142463A1 (en) 1994-04-28
MD1762B2 (ro) 2001-10-31
HUT70879A (en) 1995-11-28
PL175464B1 (pl) 1999-01-29
CZ92795A3 (en) 1995-10-18
BR9307288A (pt) 1999-05-11
GEP19981225B (en) 1998-02-12
JPH08502736A (ja) 1996-03-26
DK0665841T3 (da) 1996-08-12
EP0665841A1 (en) 1995-08-09
TJ330B (en) 2002-04-08
ATE140456T1 (de) 1996-08-15
HU9501136D0 (en) 1995-06-28
UA44695C2 (uk) 2002-03-15
DE69303721D1 (de) 1996-08-22
PL308484A1 (en) 1995-08-07
DE69303721T2 (de) 1997-01-09
RO113989B1 (ro) 1998-12-30
IL107335A0 (en) 1994-01-25
US5707933A (en) 1998-01-13
EP0665841B1 (en) 1996-07-17
US5707932A (en) 1998-01-13
SK52095A3 (en) 1995-09-13
RU95109933A (ru) 1997-01-10
AU5336594A (en) 1994-05-09
CN1086516A (zh) 1994-05-11
CA2142463C (en) 2005-01-18
CZ282171B6 (cs) 1997-05-14
SK281197B6 (sk) 2001-01-18
RU2130021C1 (ru) 1999-05-10
GR3021390T3 (en) 1997-01-31
MX9306510A (es) 1994-04-29
JP3485185B2 (ja) 2004-01-13
ZA937781B (en) 1994-05-09

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